Thionyl Chloride → 1-(4-Pyridinyl)-4-piperidinecarbonyl chloride

HRID 1882920Notes

Reaction equation

HRID 1882920 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][CH:10]([C:13]([OH:15])=O)[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.S(Cl)([Cl:18])=O>ClCCl>[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][CH:10]([C:13]([Cl:18])=[O:15])[CH2:9][CH2:8]2)=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 12682891-(Pyridin-4-yl)piperidine-4-carboxylic acid

Product 1

HCID 111837001-(4-Pyridinyl)-4-piperidinecarbonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring suspension of 1-(4-pyridinyl)piperidin-4-ylcarboxylic acid (0.8 g, 3.88 mmol) in dichloromethane (75 mL) at reflux was added thionyl chloride (0.45 mL, 5.82 mmol). After 3 h, the solvent was removed in vacuo and the residue was dissolved in dichloromethane (75 mL), giving a solution of the title compound, approximately 0.05 M.

Workup

  1. temperatureat reflux
  2. customthe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in dichloromethane (75 mL)

Sources & evidence

ORD record
ord-942fda2eebac48d18ff688a9f0edfe39
Source dataset
uspto-grants-2004_07
Patent number
US06759414B2

Reaction notes

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